N-chloro-amino acid derivatives activity

Abstract

There is provided, a novel class of compounds exhibiting antibacterial activity, said compounds having the formula: ##EQU1## wherein X and Y each represent a member which may be the same or different selected from the group consisting of H and Cl with the priviso that X and Y cannot represent H simultaneously; R 1 and R 2 each represent a member which may be the same or different selected from the group consisting of an n- or branched alkyl group of from 1 to 20 carbon atoms, an aryl group (phenyl, naphthyl, etc.) and a ##EQU2## (CH 2 ) n group, wherein n represents an integer of from 2 - 5; and Z represents a member selected from the group consisting of an --OR 3 group, a a ##EQU3## wherein R 4 and R 5 each represent a member which may be the same or different selected from the group consisting of H and an alkyl group of from 1 - 3 carbon atoms, wherein R 6 and R 7 each represent a member which may be the same or different selected from the group consisting of R 1 , R 2 , or H when X is not Cl or R 1 and R 2 when X is Cl, wherein R 1 and R 2 are defined above, wherein X is as defined above, and wherein R 3 in each case represents a member selected from the group consisting of an n- or branched alkyl group of from 2 - 20 carbon atoms, a --OCH 2 CH 2 (OCH 2 CH 2 ) n --OR 1 group, wherein R 1 is defined as above and n represents an integer of from 1 - 11, a Group, wherein W represents a member selected from the group consisting of H, an n- or branched alkyl group of from 1 - 20 carbon atoms, a halogen atom, (Cl, Br, I), an --OR 8 group, and a ##EQU4## group, wherein R 4 and R 5 are as defined above and R 8 represents a member selcted from the group consisting of H and R 1 , wherein R 1 is as defined above, and --CH 2 CH 2 --(OCH 2 CH 2 ) n -- ##SPC1## Group, wherein n represens an integer of from 1 - 20 and R 1 is as defined above, With the further proviso that when X and Y are Cl and R 1 and R 2 are methyl, Z cannot be a member selected from the group consisting of --OCH 3 and NH 2 .

What we claim is: 
     
       1. The compound: n-hexyl-α-N-chloroaminoisobutyrate. 
     
     
       2. The compound: n-octyl-α-N-chloroaminoisobutyrate. 
     
     
       3. The compound: n-dodecyl-α-N-chloroaminoisobutyrate. 
     
     
       4. The compound: n-tetradecyl-α-N-chloroaminoisobutyrate. 
     
     
       5. The compound: n-hexadecyl-α-N-chloroaminoisobutyrate. 
     
     
       6. The compound: n-octadecyl-α-N-chloroaminoisobutyrate. 
     
     
       7. The compound: Methyl-α-N,N-dichloroaminoisobutyrylglycinate. 
     
     
       8. The compound: Ethyl-α-N,N-dichloroaminoisobutyrylglycinate. 
     
     
       9. An ester of α-N,N-dichloroaminoisbutyric acid having the formula: ##SPC6## and ##EQU11##  wherein R 1  represents a member selected from the group consisting of an n- or branched alkyl group of from 1 to 20 carbon atoms, a phenyl group and a naphthyl group and wherein n represents an integer of from 1 - 11.   
     
     
       10. The compound of claim 9, wherein R 1  represents an alkyl group of from 1 to 5 carbon atoms. 
     
     
       11. An ester of α-N-chloroaminoisobutyric having the formula: ##SPC7## and ##EQU12## wherein R 1  represents a member selected from the group consisting of an n- or branched alkyl group of from 1 to 20 carbon atoms, a phenyl group and a naphthyl group, and wherein n represents an integer of from 1 to 11.   
     
     
       12. The compound of claim 11, wherein R 1  represents an alkyl group of from 1 to 5 carbon atoms.